Thermotropic delayed fluorescence material

A thermally induced delayed fluorescence, C6-C60 technology, applied in luminescent materials, electrical components, circuits, etc., can solve problems such as poor thermal stability and low glass transition temperature

Active Publication Date: 2018-03-13
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported thermally activated delayed fluorescent materials have shortcomings such as aggregation fluorescence quenching effect, low glass transition temperature and poor thermal stability in the solid state.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] A thermally induced delayed fluorescent material, namely compound CJH-16, its structural formula is as follows:

[0073]

[0074] The preparation method of above-mentioned compound CJH-16, comprises the steps:

[0075] The first step: the preparation of intermediate T-1

[0076]

[0077] 10.0g (61mmol) of 2-chloroquinoline and 11.6g (61mmol) of 4-bromothiophenol were mixed, added 200ml of water, heated and refluxed and stirred for 14 hours, cooled to room temperature, filtered, the filter cake was washed with water, and the silica gel column After separation and purification, 17.8 g of yellow solid was obtained with a yield of 92%.

[0078] The second step: the preparation of intermediate T-2

[0079]

[0080] 5g (15.8mmol) of intermediate T-1, 6.45g (17.3mmol) of intermediate T-11, 6.7g (63.2mmol) of anhydrous sodium carbonate are mixed, then add 365mg (0.316mmol) of Pd (PPh 3 ) 4 Catalyst, then add 20mL of toluene, 10mL of ethanol and 10mL of water, stir ...

Embodiment 2

[0085] A thermally induced delayed fluorescent material, namely compound CJH-42, its structural formula is as follows:

[0086]

[0087] The preparation method of above-mentioned compound CJH-42, comprises the steps:

[0088] The first step: the preparation of intermediate T-3

[0089]

[0090] 10g (41.5mmol) of 2-chloro-4-phenylquinazoline and 7.85g (41.5mmol) of 4-bromothiophenol were mixed, and intermediate T-3 was prepared according to the operation method of the first step of Example 1 , to obtain 14.7g yellow solid, yield 90%.

[0091] The second step: the preparation of intermediate T-4

[0092]

[0093] Mix 5g (23.9mmol) of 9,9-dimethylacridine and 7.4g (26.3mmol) of 4-bromoiodobenzene, add 457mg (2.4mmol) of cuprous iodide, then add 50ml of NMP, and stir Raise the temperature at 120°C for 12 hours, cool to room temperature, filter, pour the filtrate into 500ml of water, filter, wash the filter cake with water to obtain a white solid, and recrystallize with e...

Embodiment 3

[0104] A thermally induced delayed fluorescent material, namely the compound formula CJH-50, its structural formula is as follows:

[0105]

[0106] The preparation method of above-mentioned compound CJH-50, comprises the steps:

[0107] The first step: the preparation of intermediate T-7

[0108]

[0109] Mix 10g (31.6mmol) of T-1 and 100ml of glacial acetic acid, add 1ml of concentrated sulfuric acid, add 5.6g (35.0mmol) of bromine, raise the temperature to 100°C and stir for 12 hours until the red color disappears, cool to room temperature, reduce Concentrate under reduced pressure to remove glacial acetic acid, add 200 ml of ice water to the residue, extract with dichloromethane, combine the organic phases, and concentrate to dryness under reduced pressure to obtain 10 g of yellow oil with a yield of 83%.

[0110] The second step: the preparation of intermediate T-8

[0111]

[0112] 10g (25.3mmol) of T-7, 9.3g (55.6mmol) of carbazole, and 10.5g (75.9mmol) of an...

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Abstract

The invention discloses a thermotropic delayed fluorescence material, which has a general molecular formula as shown in a formula I. The formula I is shown in the description. An organic light-emitting device prepared by utilizing the material has the characteristics that the power efficiency and the external quantum efficiency of the device can be remarkably improved, the service life of a blue light device is prolonged, a material synthesis and a purification method is simple and suitable for large-scale production and the like, and is an ideal choice as an organic light-emitting device light-emitting material. The application of the organic light-emitting diode material used as a carrier transport material or independently used as a main material in a luminescent material or a luminescent layer is also within a protection range.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence display. More specifically, it relates to a thermally induced delayed fluorescent material. Background technique [0002] Organic electroluminescence (referred to as OLED) and related research As early as 1963, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display And other advantages, can be widely used in flat panel displays and surface light sources, so it has been widely research...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D401/14C07D498/04C07D491/048C07D413/12C07D239/38C07D217/22C07D413/14C07D471/04C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D217/22C07D239/38C07D401/12C07D401/14C07D413/12C07D413/14C07D471/04C07D491/048C07D498/04C09K2211/1044C09K2211/1033C09K2211/1029C09K2211/1007H10K85/649H10K85/654H10K85/657H10K85/6572H10K50/00
Inventor 曹建华隋岩董梁华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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